1-(4-クロロフェノキシ)-3,3-ジメチル-1-(1H-1,2,4-トリアゾール-1-イル)-2-ブタノール

Soluble in alcohol, ketones

In water, 120 mg/L at 20 °C

2078.6；2087.9；2076；2084；2095；2088；2104；2065.3；2063.1；2064.6；2069.9；2079.6；2062.6；2064；2087.9

2050；2069；2066.7；2061.9；2077.1；2023；2051.8

Diastereoisomer A(1RS, 2SR) and diastereoisomer B(1RS, 2RS) ratio of A:B is 7:3

Diastereoisomer A: MP = 138.2 °C; VP = 6X10-4 mPa at 20 °C; SG/Density = 1.237 g/cu cm at 22 °C; Kow (logP) = 3.08 at 25 °C; Henry's Law constant = 3X10-6 Pa cu m mol-1 at 20 °C; solubility = 62 mg/L in water at 20 °C

Diastereoisomer B: MP = 133.5 °C; VP = 4X10-4 mPa at 20 °C; SG/Density = 1.299 g/cu cm at 22 °C; Kow (logP) = 3.28 at 25 °C; Henry's Law constant = 4X10-6 Pa cu m mol-1 at 20 °C; solubility = 33 mg/L in water at 20 °C

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]；H360: May damage fertility or the unborn child [Danger Reproductive toxicity]；H362: May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]；H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P203, P260, P263, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.9% (1 of 114) of reports.

Hazard Traits - Reproductive Toxicity；Authoritative List - EC Annex VI CMRs - Cat. 1B；Report - if used as a fragrance or flavor ingredient

Commission Regulation (EC) No 1490/2002

Triadimenol is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2008/125, Reg. (EU) 2022/801, Reg. (EU) No 540/2011

Triadimenol: Does not have an individual approval but may be used under an appropriate group standard

IMAP assessments - 1H-1,2,4-Triazole-1-ethanol, .beta.-(4-chlorophenoxy)-.alpha.-(1,1-dimethylethyl)-: Human health tier I assessment；IMAP assessments - 1H-1,2,4-Triazole-1-ethanol, .beta.-(4-chlorophenoxy)-.alpha.-(1,1-dimethylethyl)-: Environment tier I assessment

Commercial material is mixture of two diastereoisomers; [Merck Index] Increased liver enzyme activity (ALT and AST) and histopathological liver changes observed in 13-week feeding study of rats at the three highest doses tested (500, 1,500, and 4,500 ppm); A 15-day dermal study of rabbits produced a NOAEL greater than highest tested dose (250 mg/kg/day); Teratogenic effects seen in tadpoles (branchial arches) and cultured rat embryos (cranial nerve and ganglia); No evidence of mutagenicity; [HSDB] Not irritating to skin or eyes of rabbits; Not sensitizing to guinea pig skin; No adverse effects to reproductive performance observed in 2-generation study of rats; No evidence of primary embryotoxic or teratogenic effects in rats or rabbits administered by gavage in the most sensitive stage of gestation; No evidence of carcinogenicity in rats or mice; [IUCLID] Repeated dose studies have shown the liver to be the target organ of toxicity (enlargement with corresponding changes in clinical chemistry); Chronic studies of rats and mice also demonstrated hepatotoxicity; Multigenerational studies produced reduced pup survival during lactation and decreased fertility index in all generations in one study; Acute triadimefon (structurally and metabolically similar fungicide) neurotoxicity studies of rats showed reversible hyperactivity and increased motor and locomotor activity without neuropathological changes; Sub-chronic studies produced consistent effects with no increase in severity observed; Does not possess potential for mutagenicity or carcinogenicity; [EFSA] See Triadimefon.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document for Triadimefon and Tolerance Reassessment for Triadimenol EPA 738-R-06-003 (August 2006). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of May 27, 2009: http://www.epa.gov/pesticides/reregistration/status.htm]

California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summary for Triadimenol (55219-65-3).[Available from, as of May 13, 2009: http://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm]

USEPA, Office of Prevention, Pesticides, and Toxic Substances; Revised HED Human Health Risk Assessment for Triadimenol (52219-65-3) (February 2006). EPA Docket No.: EPA-HQ-OPP-2006-0038-0005.

European Chemicals Bureau; IUCLID Dataset, Triadimenol (55219-65-3) (2000 CD-ROM edition).[Available from, as of May 8, 2009: http://esis.jrc.ec.europa.eu/]

Tolerances are established for the combined residues of the fungicide triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H -1,2,4-triazol-1-yl)-2-butanone, and triadimenol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-1H -1,2,4-triazole-1-ethanol, expressed as triadimefon, in or on the following food commodities: [Table#7396]

Tolerances with regional registrations, as defined in part 180.1(m), are established for the combined residues of the fungicide triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H -1,2,4-triazol-1-yl)-2-butanone, and triadimenol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-1H -1,2,4-triazole-1-ethanol, expressed as triadimefon, in or on the following food commodities: [Table#7397]

Triadimenol, a metabolite of triadimefon, is also a registered fungicide. Triadimenol was first registered after 1984 and is not subject to reregistration under the 1988 amendments to FIFRA. Triadimenol is, however, subject to tolerance reassessment under the FFDCA, as amended by FQPA. Based on its evaluation of combined exposures from the uses of triadimefon, triadimenol, and their metabolites, the Agency has determined that the tolerances for triadimefon and triadimenol are considered to be reassessed under FFDCA.

New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Triadimenol is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 127201; Type of Pesticide: conventional - fungicide; Use Site: food use, turf, ornamentals; Year: 1989.

Acute Tox. 4 (99.1%)；Acute Tox. 4 (34.2%)；Repr. 1B (26.3%)；Lact. (27.2%)；Aquatic Chronic 2 (27.2%)；Aquatic Chronic 3 (34.2%)

Acute toxicity - category 4；Reproductive toxicity - category 1B；Reproductive toxicity - effects on or via lactation；Hazardous to the aquatic environment (chronic) - category 2

Repr. 1B；Lact.；Acute Tox. 4；Aquatic Chronic 2

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans, or other waters unless in accordance with the requirements of a National Pollutant Discharge Elimination System (NPDES) permit and the permitting authority has been notified in writing prior to discharge.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Discard clothing and other absorbent materials that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them.

Users should wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet.

For more Preventive Measures (Complete) data for Triadimenol (13 total), please visit the HSDB record page.

Tolerances are established for the combined residues of the fungicide triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H -1,2,4-triazol-1-yl)-2-butanone, and triadimenol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-1H -1,2,4-triazole-1-ethanol, expressed as triadimefon, in or on the following food commodities: [Table#7394]

Tolerances with regional registrations, as defined in part 180.1(m), are established for the combined residues of the fungicide triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H -1,2,4-triazol-1-yl)-2-butanone, and triadimenol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-1H -1,2,4-triazole-1-ethanol, expressed as triadimefon, in or on the following food commodities: [Table#7395]

Water soluble packets when used correctly qualify as a closed mixing/loading system under the Worker Protection Standard for Agricultural Pesticides [40 CFR 170.240(d)(4)]. Mixers and loaders using water soluble packets must: wear the personal protective equipment required on this labeling for mixers and loaders, and be provided, have immediately available, and wear in an emergency, such as a broken package, spill, or equipment breakdown: chemical resistant footwear and a NIOSH-approved respirator equipped with a dust/mist filter with MSHA/NIOSH approval number prefix TC-21C or any N, R, P, or HE filter.

Mixers, loaders, applicators, flaggers, and other handlers must wear long sleeved shirt and long pants, shoes plus socks, and chemical resistant gloves when mixing/loading, when applying using handheld equipment or handheld nozzles, or when handling treated seed (including spreading, drying, raking, bagging, and sewing seed bags).

... Doses of 15 and 60 mg/kg /triadimenol/ potentiated the effect of amphetamine while doses of 12 to 48 mg/kg antagonized the reserpin response. Triadimenol also prolonged the hexobartital sleeping time at 15 and 60 mg/kg.

... Rats exposed to 48 mg/kg triadimenol elicited an excitatory effect. A comparison with caffeine (doses of 2.5 and 10 mg/kg) showed that the effect of 2.5 mg/kg caffeine corresponded approximately to that of 12 to 15 mg/kg KWG 0519, in the amphetamine potentiation test 2.5 mg/kg caffeine elicited a similar response as 4 mg/kg KWG 0519, while in the antagonism of ptosis 10 mg/kg caffeine and 12 mg/kg KWG 0519 were comparable. The noeffect dose was 1 mg/kg for caffeine. The findings of this study point to a potential for stimulation of Central Nervous System (CNS).

LC50; Species: Anas platyrhynchos (Mallard duck, age 13 days) diet >5000 ppm for 8 days

LC50; Species: Colinus virginianus (Northern bobwhite) diet >2000 ppm for 8 days

LC50; Species: Colinus virginianus (Northern bobwhite, age 16 days) diet >5000 ppm for 8 days

LD50; Species: Serinus canaria (Island canary) oral >1000 mg/kg

For more Ecotoxicity Values (Complete) data for Triadimenol (11 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 211(2) to 992(3) indicate that triadimenol is expected to have moderate to low mobility in soil(SRC). Volatilization of triadimenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-12 atm-cu m/mole(SRC), based upon its vapor pressure, 3.1X10-10 mm Hg(4), and water solubility, 120 mg/L(5). Triadimenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure(4). In soil, triadimefon degraded with a half life of 15 days to form triadimenol, which was found to be fairly persistent in accord with other compounds that contain triazole groups(6).

TERRESTRIAL FATE: Numerous field studies indicated the presence of triadimenol following the application of triadimefon. Triadimenol residues in soil have been detected after several years of application. Based on one apple orchard trial, triadimenol can consist of 0.13-0.65 mg/kg in the 0-10 cm layer soil during 5 years. The half-life value for triadimenol was determined to range from 3-months to 500 days and consequently thought of as a persistent compound in soil. Often triadimefon and triadimenol are quantified together; however, crop studies specifically detected triadimenol in apples, grapes, melons, strawberries, tomatoes, and wheat at levels up to 0.52 mg/kg at 42 days. 14-C-Radiolabeling studies of 14-C triadimefon treated crops indicated a triadimenol 14-C recovery of 0-1% from barley, 6-23% from wheat, and 25% from apples(1).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 211(2) to 992(3), indicate that triadimenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.3X10-12 atm-cu m/mole(SRC), derived from its vapor pressure, 3.1X10-10 mm Hg(5) and water solubility, 120 mg/L(6). According to a classification scheme(7), an estimated BCF of 21(SRC), from a log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Triadimenol adsorbed on sediments of a pond had a half-life 110-375 days(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triadimenol, which has a vapor pressure of 3.1X10-10 mm Hg at 25 deg(2) is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase triadimenol may be removed from the air by wet or dry deposition(SRC). Triadimenol contains chromophores that absorb at wavelengths >290 nm(3); it undergoes some photodegradation upon solar radiation, at a rate of 2.8X10-2 umol/sq cm-hr(4).

/AQUATIC SPECIES/ Conazole fungicides are commonly used to prevent fungal growth on turf grass and agricultural crops. As many of these sites are adjacent to coastal waterways and estuaries, there exists the potential for nontarget effects of runoff on marine organisms. This study reports 96 hr EC(50) values for four selected conazole fungicides (triadimefon = 5.98 mg/L; triadimenol = 5.51 mg/L; propiconazole = 2.33 mg/L; hexaconazole = 0.91 mg/L) to the model test alga Dunaliella tertiolecta. We further investigated possible mechanisms of toxicity by examining sublethal effects of exposure on cell morphology, osmoregulatory function, and lipid composition. These mechanistic studies revealed that conazole exposure does not inhibit synthesis of the cell's glycerol osmolyte, but does result in an overall increase in cellular volume and total lipid content. Both fungi and chlorophytes rely on ergosterol to maintain membrane structure and fluidity, and we provide evidence that the sterol-inhibiting conazoles may interfere with ergosterol biosynthesis in the cell membrane of Dunaliella. ...

/AQUATIC SPECIES/ ... A rainbow trout (Oncorhynchus mykiss) microsomal aromatase assay /was optimized/ to measure the effects of 43 substances ... on brain and ovarian aromatase activities in vitro. ... 12 compounds were able to inhibit brain and ovarian aromatase activities in a dose-dependent manner with IC50 values ranging from the low nM to the high uM range depending on the substance: steroidal and non steroidal inhibitors of aromatase (4-hydroxyandrostenedione, androstatrienedione, aminogluthethimide), imidazole fungicides (clotrimazole, imazalil, prochloraz), triazole fungicides (difenoconazole, fenbuconazole, propiconazole, triadimenol), the pyrimidine fungicide fenarimol and methylmercury...

At Kentville, Nova Scotia, Canada, seeds of Lennox winter wheat were treated with triadimenol at the rate of 0.3 g a.i./kg, and planted on September 18. Samples of green foliage were taken November 23 and analyzed for triadimenol on May 7 and June 14 of the following year. Residues of triadimenol at the first, second and third sampling dates averaged 0.05, 0.02 and 0.02 ppm, respectively. In another study, Lennox winter wheat treated with triadimenol at the rate of 0.3 g a.i./kg seed on August 26, was planted on September 4; samples of foliage taken November 16 found 0.03 ppm triadimenol in the foliage(1).

Residues of triadimefon, including triadimenol, have been determined in extensive trials on growing cereal plants, e.g. barley, oat and wheat. The majority of residue is in the converted triadimenol form at day 14(1).

In Germany, triadimenol sediment was sampled at depths of 0-15 cm depth from the pond and analyzed; Kf = 8.3, Kd = 7.6, and Koc = 211 were calculated for triadimenol(1). Koc values were estimated for triadimenol using soil samples from various European sites as follows: Sicily, Italy (992, clay), Peloponnesos, Greece (161, silt loam), Wales, U.K. (231, loam), Normandy, France (150, silt), and Schleswig-Holstein, Germany (568, loamy sand)(2). According to a classification scheme(3), these Koc values suggest that triadimenol is expected to have low to moderate mobility in soil.

/SURVEILLANCE/ ... Of the 46 non-occupational exposures /reported to the Poison Control Center between 1993 and 1998/, 13 occurred in children under six years of age. Of the total 20 cases with medically determined outcome, 11 reported minor medical outcome. Of the total 54 exposures to triadimefon/triadimenol, just four were seen in a health care facility and none required hospitalization. A review of symptoms revealed almost exclusively irritation effects (including rash and erythema) to skin, mouth, throat, and eyes. These effects were reported a total of 24 times with some patients reporting two or more of these symptoms. There were four cases reporting headache and two reported cough. No other significant symptoms were reported.

/SURVEILLANCE/ /According to the California Department of Pesticide Regulation, following exposure to triadmefon/triadimnol/ foliar residues accounted for half of the illnesses and nearly half of the systemic illnesses. Although most of the symptoms appeared to be minor, skin and eye irritation, and rash were among the most common topical symptoms. The most common systemic effects included nausea, headache, sneezing, congestion, difficulty breathing and other allergic-type reactions. There were three reports of vomiting.

/ENDOCRINE MODULATION/ Estrogenic activities of 20 selected pesticides ... were examined by estrogen receptor (ER)-dependent MCF-7 cell proliferation assay. Among them, chlordecone, dicofol, methoxychlor, gamma-HCH, fenarimol, EPN, triadimefon, and triadimenol had estrogenic activities, all of which were suppressed by the addition of pure antiestrogen ICI 182,780. ... The antiestrogenic activity of a compound was examined by estimating its suppressive effect on cell proliferation induced by 30 pM 17beta-estradiol. Strongly suspected antiestrogens were captan and myclobutanil ... . Antiestrogenic activities of nitrofen, fenitrothion, fenarimol and triadimefon were also suggested...

Triadimenol's production may result in its release to the environment through various waste streams; its use as a systemic fungicide(1) will result in its direct release to the environment(SRC). In soil, triadimefon degraded with a half-life of 15 days to form triadimenol(2).

An estimated BCF of 21 was calculated for triadimenol (SRC), using its log Kow of 2.90(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Hazard Traits - Reproductive Toxicity；Authoritative List - EC Annex VI CMRs - Cat. 1B；Report - if used as a fragrance or flavor ingredient

Commission Regulation (EC) No 1490/2002

Triadimenol is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2008/125, Reg. (EU) 2022/801, Reg. (EU) No 540/2011

Triadimenol: Does not have an individual approval but may be used under an appropriate group standard

Tolerances are established for the combined residues of the fungicide triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H -1,2,4-triazol-1-yl)-2-butanone, and triadimenol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-1H -1,2,4-triazole-1-ethanol, expressed as triadimefon, in or on the following food commodities: [Table#7396]

Tolerances with regional registrations, as defined in part 180.1(m), are established for the combined residues of the fungicide triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H -1,2,4-triazol-1-yl)-2-butanone, and triadimenol, beta-(4-chlorophenoxy)-alpha-(1,1-dimethylethyl)-1H -1,2,4-triazole-1-ethanol, expressed as triadimefon, in or on the following food commodities: [Table#7397]

Triadimenol, a metabolite of triadimefon, is also a registered fungicide. Triadimenol was first registered after 1984 and is not subject to reregistration under the 1988 amendments to FIFRA. Triadimenol is, however, subject to tolerance reassessment under the FFDCA, as amended by FQPA. Based on its evaluation of combined exposures from the uses of triadimefon, triadimenol, and their metabolites, the Agency has determined that the tolerances for triadimefon and triadimenol are considered to be reassessed under FFDCA.

New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Triadimenol is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 127201; Type of Pesticide: conventional - fungicide; Use Site: food use, turf, ornamentals; Year: 1989.

Triazole-derivatives alter the pharyngeal apparatus morphogenesis of rodent embryos cultured in vitro. The hindbrain segmentation and the rhombencephalic neural crest cell (NCCs) migration are altered by Fluconazole exposure in vitro. The aim of the present work is to identify if a common pathogenic pathway is detectable also for other molecules of this class of compounds. 9.5 days post coitum (d.p.c.) old rat embryos were exposed in vitro to the teratogenic concentrations of Flusilazole, Triadimefon and Triadimenol and cultured for 24, 48 or 60 hr. The expression and localization of Hox-b1 and Krox-20 proteins (used as markers for hindbrain segmentation) were evaluated after 24 hr of culture. The localization and distribution of NCC was evaluated after 24, 30 and 48 hr of culture. The morphology of the embryos was analyzed after 48 hr, while the branchial nerve structures were evaluated after 60 hr of culture. Hindbrain segmentation and NCC migration alteration as well as pharyngeal arch and cranial nerve abnormalities were detected after exposure of the tested molecules. A common severe teratogenic intrinsic property for the tested molecules of this chemical class has been found, acting through alteration of the normal hindbrain developmental pattern.

Triazole fungicide pesticides, in general, are believed to exhibit their fungicidal activity through an inhibition of ergosterol biosynthesis, leading to an inhibition of cell wall precursors. /Researchers/ evaluated the potential for 14 triazole fungicides and structurally related compounds ... /Research/ showed that of the chemicals tested, only triadimefon and triadimenol were able to induce hyperactivity /in the CNS/; none of the other triazoles or related compounds tested produced this effect. The author hypothesized that the ether oxygen component of the triadimenol and triadimefon molecules appears to be an important structural requirement for induction of hyperactivity in rats. As such, at this time, although the fungicidal activity of triadimefon and triadimenol may be through the inhibition of sterol synthesis, the primary mode of toxicity in mammals appears to be neurotoxicity mediated through an indirect monoaminergic mechanism that appears to be specific to triadimefon and triadimenol only./Triazole fungicides/

The mode of toxic action for triadimenol involves blocking the re-uptake of dopamine. These pesticides act as indirect dopamine agonists by binding to the dopamine transporter and increasing levels of synaptic dopamine.

... In studies conducted with rat hepatic microsomes, triadimenol was identified as the major metabolite (approximately 80%) of triadimefon metabolism, and reduction of the carbonyl group in triadimefon occurred stereoselectively with preferential formation of the less toxic triadimenol B diastereomer...

Triadimefon, triadimenol, and other triazole fungicides are metabolized in animals and plants to form compounds containing the triazole moiety, including 1,2,4-triazole (free triazole), triazole alanine, and triazole acetic acid, which are also considered in this decision ...

... A lactating goat received [phenyl-(14)C]triadimefon at 86.4 ppm for three consecutive days in feed. Triadimefon was detected at low levels in milk and fat (<5% TRR) but was not detected in kidney, liver, or muscle. The major residue identified was KWG 1342 glucuronide (6-47% TRR). Triadimenol and its conjugates comprised a major portion of the residue in tissues and milk (totals of 9-42% TRR). The remainder of the radioactivity was identified as KWG 1323 glucuronide (19-22% TRR) and KWG 1342 (1-6% TRR) and its sulfate (1-15% TRR in tissues, 43% TRR in milk). /Triadimefon/

... 16 laying hens received [phenyl-(14)C]triadimefon at 28.7 ppm for three consecutive days in feed. Triadimefon was identified in fat and eggs (4-17% TRR) but was not detected in liver or muscle. Triadimenol and its related compounds were the major metabolites identified (totals of 41-49% TRR). The remainder of the radioactivity was identified as KWG 1342 and its related compounds (totals of 10-36% TRR), p-chlorophenol (liver and fat only at 2- 4% TRR), chlorophenoxytriazolyl acetic acid (muscle only at 3% TRR), and KWG 1323 (eggs and fat only at 3-5% TRR). /Triadimefon/

... 16 laying hens received [phenyl-(14)C]triadimefon at 28.7 ppm for three consecutive days in feed. Triadimefon was identified in fat and eggs (4-17% TRR) but was not detected in liver or muscle. Triadimenol and its related compounds were the major metabolites identified (totals of 41-49% TRR). The remainder of the radioactivity was identified as KWG 1342 and its related compounds (totals of 10-36% TRR), p-chlorophenol (liver and fat only at 2- 4% TRR), chlorophenoxytriazolyl acetic acid (muscle only at 3% TRR), and KWG 1323 (eggs and fat only at 3-5% TRR). /Triadimefon/

Single oral doses of 25 mg/kg /triadimenol/ were administered to rats. Label was fairly readily excreted (over 70% in a week). In males, label was distributed 30% in urine and 53% in feces: in females distribution was 40% and 35%, respectively. No activity was found in expired gases. The major identified band in urine and in feces was KWG 0519 acid (formed by oxidation of the isobutyl moiety of triadimenol]. KWG 0519 (two isomers are present) was more abundant in plasma and in liver than the original Bayleton. Prevalence of KWG 0519 isomers was particularly apparent in males.

Used as an agricultural fungicide and seed protectant; [Merck Index] The major metabolite of the triazole fungicide triadimefon; A broad spectrum systemic fungicide used as seed treatment for barley, corn, cotton, oats, rye, sorghum, and wheat; An import tolerance is also set for bananas; [Reference #1] Used as fungicide for table and wine grapes, cereals, and cereal seed treatment in the EU; [EFSA]

Farming (Pesticides) [Category: Industry]

For triadimenol (USEPA/OPP Pesticide Code: 127201) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Used as a seed treatment on: barley, corn, cotton, oats, rye, sorghum, and wheat. There is also an import tolerance on bananas.

Baytan: Seed treatment to control smut and bunt of wheat, loose and covered smut and Typhula blight of barley, powdery mildew, rust, leaf spot and take-all and root and foot rot of wheat and barley; head smut of corn and grain sorghum. Bayfidan: Foliar treatments to control powdery mildew, rust, and Rhynchosporium in cereal. On cotton for protection against Rhizoctonia and Thielaviopsis. Also used on vegetables, ornamentals, coffee, deciduous fruit, grapes, tobacco, bananas, and other crops. Shavit: Seed treatment to control smut, ergot, snow mold, spot blotch, bunt, and Rhynchosporium in cereal; head smut of corn and sorghum; foliar treatment to control rust; powdery mildew in deciduous fruit, grapes, mango, ornamentals and vegetables.

Systemic fungicide registered for use in the United States as a seed treatment for barley, corn, cotton, oats, rye, sorghum, and wheat.

Triadimenol is produced by reduction of triadimefon with aluminum isopropoxide.

Preparation BE 814831; W. Kramer et al., US 3952002 (1974,1976 both to Bayer AG).

Registered formulations include emulsifiable concentrate (EC) (5% active ingredient), wettable powder (WP)(25% active ingredient), soluble concentrate (SC) (13.33% active ingredient), and flowable concentrate (FlC) (28.3 - 30% active ingredient).

Emulsifiable concentrate, flowable, granule, seed dressing, water dispersible granule, water-oil emulsion, wettable powder.

Baytan Technical; Active ingredient 98.30% Triadimenol

Gustafson RTU-Baytan-Thiram Fungicide; Active ingredients 15.30% Thiram and 5.00% Triadimenol

For more Formulations/Preparations (Complete) data for Triadimenol (7 total), please visit the HSDB record page.

Fungicides, Transformation products

Environmental transformation -> Pesticides (parent, predecessor)

The WHO Recommended Classification of Pesticides by Hazard identifies Triadimenol (technical grade) as Class III: slightly hazardous; Main Use: Fungicide, for seed treatment.

Commercial product is mixture of 2 diastereoisomers.